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Volumn 67, Issue 51, 2011, Pages 9853-9869

Methodological advances permit the stereocontrolled construction of diverse fully synthetic tetracyclines containing an all-carbon quaternary center at position C5a

Author keywords

Cyclopropane ring opening; Enone synthesis; Michael Claisen cyclization; Quaternary center; Tetracycline

Indexed keywords

CYCLOPROPANE; DITHIOL DERIVATIVE; LITHIUM DERIVATIVE; NUCLEOPHILE; TETRACYCLINE DERIVATIVE;

EID: 81255127418     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.09.143     Document Type: Article
Times cited : (26)

References (49)
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    • While the introduction of new substituents at C5a would not be expected to significantly affect affinity for the bacterial ribosome (based on analysis of crystal structures), such modifications could certainly influence processes, such as cell penetration and susceptibility to resistance mechanisms
    • While the introduction of new substituents at C5a would not be expected to significantly affect affinity for the bacterial ribosome (based on analysis of crystal structures), such modifications could certainly influence processes, such as cell penetration and susceptibility to resistance mechanisms: R. O'Shea, and H.E. Moser J. Med. Chem. 51 2008 2871 2878
    • (2008) J. Med. Chem. , vol.51 , pp. 2871-2878
    • O'Shea, R.1    Moser, H.E.2
  • 33
    • 0004351890 scopus 로고    scopus 로고
    • Wiley New York p. 704
    • Org. Synth. Collect. Vol. 9 1998 Wiley New York p. 704
    • (1998) Org. Synth. , vol.9
  • 38
    • 0043104432 scopus 로고
    • For an overview, see: 'Electrophilic Cyclopropanes in Organic Synthesis'
    • For an overview, see: 'Electrophilic Cyclopropanes in Organic Synthesis' S. Danishefsky Acc. Chem. Res. 12 1979 66 72
    • (1979) Acc. Chem. Res. , vol.12 , pp. 66-72
    • Danishefsky, S.1
  • 45
    • 0032512085 scopus 로고    scopus 로고
    • The hydrogenolysis deprotection step (typically the final step) was slow and low-yielding in the presence of primary and secondary amines. To synthesize the amines 32 and 34 most efficiently the usual order of deprotection steps was reversed and the hydrogenolysis reaction was performed on substrates in which primary or secondary amines were protected as tert-butyl carbamates. For discussion of the inhibitory effects of amines on Pd-catalyzed hydrogenolysis, see
    • The hydrogenolysis deprotection step (typically the final step) was slow and low-yielding in the presence of primary and secondary amines. To synthesize the amines 32 and 34 most efficiently the usual order of deprotection steps was reversed and the hydrogenolysis reaction was performed on substrates in which primary or secondary amines were protected as tert-butyl carbamates. For discussion of the inhibitory effects of amines on Pd-catalyzed hydrogenolysis, see: H. Sajiki, and K. Hirota Tetrahedron 54 1998 13981 13996
    • (1998) Tetrahedron , vol.54 , pp. 13981-13996
    • Sajiki, H.1    Hirota, K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.